2-[[4-(1H-Imidazol-1-yl)butyl]thio]-5-chlorobenzothiazole

ID: ALA3415252

PubChem CID: 118733130

Max Phase: Preclinical

Molecular Formula: C14H14ClN3S2

Molecular Weight: 323.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Clc1ccc2sc(SCCCCn3ccnc3)nc2c1

Standard InChI:  InChI=1S/C14H14ClN3S2/c15-11-3-4-13-12(9-11)17-14(20-13)19-8-2-1-6-18-7-5-16-10-18/h3-5,7,9-10H,1-2,6,8H2

Standard InChI Key:  YPPJXYVWXQGEMP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   -2.3155    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028   -1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0028    1.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917    0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2917   -0.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138   -1.2033    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5889    0.0182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7138    1.2033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0872    0.0382    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.8208    1.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3215    1.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0552    2.6770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5559    2.6972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2896    4.0065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7682    4.1664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0582    5.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7481    6.3687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6485    5.3485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3560    1.3452    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 15  1  0
  1 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3415252

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 323.87

Molecular Weight (Monoisotopic): 323.0318

AlogP: 4.72

#Rotatable Bonds: 6

Polar Surface Area: 30.71

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.54

CX LogP: 4.41

CX LogD: 4.37

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.49

Np Likeness Score: -2.68

References

1. Salerno L, Pittalà V, Romeo G, Modica MN, Marrazzo A, Siracusa MA, Sorrenti V, Di Giacomo C, Vanella L, Parayath NN, Greish K..  (2015)  Novel imidazole derivatives as heme oxygenase-1 (HO-1) and heme oxygenase-2 (HO-2) inhibitors and their cytotoxic activity in human-derived cancer cell lines.,  96  [PMID:25874340] [10.1016/j.ejmech.2015.04.003]

2. Salerno L, Amata E, Romeo G, Marrazzo A, Prezzavento O, Floresta G, Sorrenti V, Barbagallo I, Rescifina A, Pittalà V..  (2018)  Potholing of the hydrophobic heme oxygenase-1 western region for the search of potent and selective imidazole-based inhibitors.,  148  [PMID:29454190] [10.1016/j.ejmech.2018.02.007]

Source

Source(1):

• Scientific Literature